Normetanefrina

Normetanefrina
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Nome IUPAC 4-(2-amino-1-hydroxy-ethyl)- 2-methoxy-phenol
Identificadores
Número CAS 97-31-4
PubChem 1237
ChemSpider 1200
MeSH Normetanephrine
SMILES
InChI
1/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3
Propriedades
Fórmula molecular C9H13NO3
Massa molar 183,204 g/mol
Página de dados suplementares
Estrutura e propriedades n, εr, etc.
Dados termodinâmicos Phase behaviour
Solid, liquid, gas
Dados espectrais UV, IV, RMN, EM
Exceto onde denotado, os dados referem-se a
materiais sob condições normais de temperatura e pressão
Referências e avisos gerais sobre esta caixa.
Alerta sobre risco à saúde.

Normetanefrina, 4-(2-amino-1-hidroxi-etil)-2-metoxi-fenol, é um metabólito intermediário do metabolismo da catecolamina, metabólito da norepinefrina criado pela ação da catecol O-metiltransferase (catecol-O-metilase) sobre a norepinefrina. É excretada na urina e encontrada em certos tecidos. [1][2]

Tanto a normetanefrina quanto a metanefrina são excretadas na urina e sua dosagem os torna um marcador para tumores secretores de catecolamina, como feocromocitoma. Juntamente com a metanefrina, representa 20-40% dos catabólitos urinários decorrentes do metabolismo da catecolamina. É um marcador para tumores secretores de catecolamina tais como o feocromocitoma.[3]


Degradação da norepinefrina. Normetanefrina é mostrada no canto superior esquerdo. As enzimas são mostradas em caixas.[4]

Marcador tumoral

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Os valores normais de metanefrina e normetanefrina, tomando-se como referência a urina de 24 horas, estão entre 310-510 µg / 24, seu aumento está associado ao aparecimento de feocromocitomas, sendo falso-positivos possíveis, pois os valores dessas moléculas no sangue também podem aumentar após tratamentos com IMAO, catecolaminas, L-Dopa, betabloqueadores e em indivíduos que sofrem de etilismo crônico.[5][6][7][8][9][10][11]

Referências

  1. ↑ D. Andreani,G. Menzinger, D. Andreani; (1984) "Trattato di diagnostica funzionale endocrinologica" ISBN 88-299-0196-2
  2. ↑ Kambur O, Kaunisto MA, Tikkanen E, Leal SM, Ripatti S, Kalso EA. Effect of catechol-o-methyltransferase-gene (COMT) variants on experimental and acute postoperative pain in 1,000 women undergoing surgery for breast cancer. Anesthesiology. 2013 Dec;119(6):1422-33. doi: 10.1097/ALN.0000000000000013.
  3. ↑ M. Mannelli1, T. Ercolino1, L. Becherini1, G. Bernini2, L. Simi1, G. Parenti1; Ligand Assay (2006); "Diagnosi genetica e biochimica del ferocromocitoma"
  4. ↑ Figura 11-4 em: Flower, R.; Rang, H. P.; Dale, M. M.; Ritter, J. M. (2007). Rang & Dale's Pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-06911-5 
  5. ↑ Brain, K. L., Kay, J., & Shine, B. (2006). Measurement of urinary metanephrines to screen for pheochromocytoma in an unselected hospital referral population. Clinical chemistry, 52(11), 2060–2064.
  6. ↑ Oishi S, Sasaki M, Ohno M, Sato T. Urinary normetanephrine and metanephrine measured by radioimmunoassay for the diagnosis of pheochromocytoma: utility of 24-hour and random 1-hour urine determinations. J Clin Endocrinol Metab. 1988 Sep;67(3):614-8.
  7. ↑ Eisenhofer, G., Walther, M., Keiser, H.R., Lenders, J.W.M., Friberg, P., & Pacak, K.. (2000). Plasma metanephrines: a novel and cost-effective test for pheochromocytoma. Brazilian Journal of Medical and Biological Research, 33(10), 1157-1169.
  8. ↑ Ogata M, Mendelson JH, Mello NK, Majchrowicz E. Adrenal function and alcoholism. II. Catecholamines.Psychosom Med. 1971 Mar-Apr;33(2):159-80. PMID: 5549660 DOI: 10.1097/00006842-197103000-00007
  9. ↑ Recent Advances in Studies of Alcoholism: An Interdisciplinary Symposium; National Institute on Alcohol Abuse and Alcoholism, 1971. pág. 152.
  10. ↑ Charles S. Lieber; Metabolic Aspects of Alcoholism. Springer Science & Business Media, 2012. pág. 266.
  11. ↑ Bulletin, Problems of Drug Dependence: Report of the Thirty-first Meeting, 24, 25, and 26 February, 1969, Palo Alto, California. National Research Council (U.S.). Committee on Problems of Drug Dependence. pág. 6276.

Bibliografia

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  • Anton AH, Sayre DF. J Pharmacol Exp Ther. 1966 Jul;153(1):15-29. Distribution of metanephrine and normetanephrine in various animals and their analysis in diverse biologic material. PMID 5921354
  • Sato T, Yoshinaga K. Tohoku J Exp Med. 1973 Jul;110(3):283-7. A metanephrine test for a screening of catecholamine-producing tumors. PMID 4757670
  • Eisenhofer G, Lenders JW. Adv Pharmacol. 1998;42:374-7. Clues to the diagnosis of pheochromocytoma from the differential tissue metabolism of catecholamines. PMID 9327920
  • Shimbo S. Naika Hokan. 1968 Sep;15(9):299-310. Japanese. Clinical studies on urinary metanephrine and normetanephrine in various endocrine diseases. 2. Clinical studies on urinary metanephrine and normetanephrine in patients with pheochromyocytoma and a patient with neuroblastoma. PMID 5752086
  • Wolf RL, Gherman CE, Lauer JD, Fish HL, Levey BR. Clin Sci Mol Med Suppl. 1973 Aug;45 Suppl 1:263s-7. A new urinary assay for separate normetanephrine and metanephrine with application for the diagnosis of phaeochromocytoma. PMID 4522173
  • Griffin A, O'Shea P, FitzGerald R, O'Connor G, Tormey W. Ann Clin Biochem. 2011 Jan;48(Pt 1):41-4. Epub 2010 Dec 1. Establishment of a paediatric age-related reference interval for the measurement of urinary total fractionated metanephrines. PMID 21123298
  • Iwaoka T, Umeda T, Sato T. Nippon Rinsho. 1989 Dec;48 Suppl:1186-9. Japanese. Clinical significance of metanephrine and normetanephrine analysis in endocrine tests of the adrenal medulla and sympathetic nervous system. PMID 2621844
  • Käser H, Türler K, Burri PH. Schweiz Med Wochenschr. 1971 Apr 3;101(13):484-7. German. Catecholamine metabolism in the tissue of malignant and benign tumors of the sympathetic nervous system. PMID 5558918
  • Murakami M, Tomita K. Nippon Rinsho. 1999 Dec;57 Suppl:219-22. Review. Japanese. Metanephrine (M) and normetanephrine (NM). PMID 10778105
  • Bertani LM, Dziedzic SW, Clarke DD, Gitlow SE. Clin Chim Acta. 1970 Nov;30(2):227-33. A gas-liquid chromatographic method for the separation and quantitation of normetanephrine and metanephrine in human urine. PMID 5478310
  • Yaworsky DC, Wu AH, Hill DW. Clin Chim Acta. 2005 Mar;353(1-2):31-44. The use of plasma metanephrine to normetanephrine ratio to determine epinephrine poisoning. PMID 15698588
  • Eisenhofer G, Lenders JW, Goldstein DS, Mannelli M, Csako G, Walther MM, Brouwers FM, Pacak K. Clin Chem. 2005 Apr;51(4):735-44. Epub 2005 Feb 17. Pheochromocytoma catecholamine phenotypes and prediction of tumor size and location by use of plasma free metanephrines. PMID 15718487
  • Lando LI, Krupenina LB, Aziavchik AV. Vopr Med Khim. 1973 Sep-Oct;19(5):501-5. Russian. Adrenaline and noradrenaline concentrations in rat tissues in different phases of single and repeated electroconvulsive seizures. PMID 4788174
  • Raum WJ. Methods Enzymol. 1987;142:550-71. Enzymatic radioimmunoassay of epinephrine, norepinephrine, metanephrine, and normetanephrine. PMID 3600381
  • Steinberg AB. Biol Psychol. 1974;2(2):135-49. Individual patterns of excretion of metanephrine and normetanephrine by children. PMID 4475599
  • Bigelow LB, Dairman W, Weil-Malherbe H, Udenfriend S. Mol Pharmacol. 1969 Nov;5(6):565-71. Increased synthesis of catecholamines and their metabolites following the administration of phenoxybenzamine. PMID 5373892
  • Canfell C, Binder SR, Khayam-Bashi H. Clin Chem. 1982 Jan;28(1):25-8. Quantitation of urinary normetanephrine and metanephrine by reversed-phase extraction and mass-fragmentographic analysis. PMID 7055927
  • Iwata H, Fujimoto S, Nishikawa T, Hano K. Experientia. 1968 Apr 15;24(4):378-80. German. Pharmacologic studies in thiamine deficiency. I. Changes in the catecholamine content of tissues. PMID 5705198
  • Miyoshi T, Tomita K.Nippon Rinsho. 2005 Aug;63 Suppl 8:395-8. Review. Japanese. Metanephrine (M), normetanephrine (NM) and fractionated metanephrines PMID 16149538